This invention relates to N-substituted-N'-substituted-N,N'-diacylhydrazines which are useful as insecticides, compositions containing those compounds and methods of their use.
The search for compounds which have a combination of excellent insecticidal activity and low undesirable toxicity is a continuing one because of factors such as the desire for compounds exhibiting greater activity, better selectivity, low undesirable environmental impact, low production cost and effectiveness against insects resistant to many known insecticides.
Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.
Certain hydrazine derivatives have been disclosed in the literature.
In 25 Aust. J. Chem., 523-529 (1972), several N,N'-dibenzoylhydrazine derivatives are disclosed in which one or both nitrogen atoms are alkylated or phenylated. No biological activity is disclosed for those compounds.
In 61 Helv. Chim. Acta, 1477-1510 (1978), several N,N'-dibenzoylhydrazine derivatives are disclosed. No biological activity is disclosed for those compounds.
In 44 J.A.C.S., 2556-2567 (1922), isopropyl hydrazine (CH.sub.3).sub.2 CH-NH-NH.sub.2, symmetrical diisopropyl hydrazine, dibenzoylisopropyl hydrazine and certain derivatives are disclosed. No biological activity is disclosed for those compounds.
In 44 J.A.C.S., 1557-1564 (1972), isopropyl, menthyl and bornyl semicarbazides are disclosed. No biological activity is disclosed for those compounds.
In 48 J.A.C.S., 1030-1035 (1926), symmetrical di-methylphenylmethyl hydrazine and certain related compounds including 1,2-bis-methylphenylmethyl-4-phenylsemicarbazide are disclosed. No biological activity is disclosed for those compounds.
In 27 Bull. Chem. Soc. Japan, 624-627 (1954), certain hydrazine derivatives including alpha, beta-dibenzoylphenyl hydrazine are disclosed. No biological activity is disclosed for those compounds.
In J. Chem. Soc. (C), 1531-1536 (1966), N,N'-dibenzoylphenyl hydrazine and N-acetyl-N'-benzoyl-p-nitro-phenyl hydrazine are disclosed. No biological activity is disclosed for those compounds.
In 56B Chem. Berichte, 954-962 (1923), symmetrical di-isopropyl hydrazines, symmetrical diisobutyl and certain derivatives including N,N'-diisobutyldibenzoyl hydrazine are disclosed. No biological activity is disclosed for those compounds.
In 590 Annalen der Chemie, 1-36 (1954), certain N,N'-dibenzoyl hydrazine derivatives are disclosed including N'-methyl- and N'-(2-phenyl)-isopropyl-N,N'-dibenzoyl hydrazine. No biological activity is disclosed for those compounds.
In J. Chem. Soc., 4191-4198 (1952), N,N'-di-n-propyl hydrazine and the bis-3,5-dinitrobenzoyl derivatives are disclosed. No biological activity is disclosed for those compounds.
In 32 Zhur. Obs. Khim., 2806-2809 (1962), N'-2,4-methyl-2,4-pentadiene-N,N'-dibenzoyl hydrazine is disclosed. No biological activity is disclosed.
In 17 Acta. Chim. Scand., 95-102 (1963), 2-benzoyl-thiobenzhydrazide (C.sub.6 H.sub.5 --CS--NHNH--CO--C.sub.6 H.sub.5) and certain hydrazone and hydrazine derivatives are disclosed including 1,2-dibenzoyl-benzyl hydrazine. No biological activity is disclosed for those compounds.
In 25 Zhur. Obs. Khim, 1719-1723 (1955), N,N'-bis-cyclohexyl hydrazine and N,N'-dibenzoylcyclohexyl hydrazine are disclosed. No biological activity is disclosed for those compounds.
In J. Chem. Soc., 4793-4800 (1964), certain dibenzoyl hydrazine derivatives are disclosed including tribenzoyl hydrazine and N,N'-dibenzoylcyclohexyl hydrazine. No biological activity is disclosed for those compounds.
In 36 J. Prakt. Chem., 197-201 (1967), certain dibenzoyl hydrazine derivatives including N'-ethyl-; N'-n-propyl; N'-isobutyl-; N'-neopentyl-; N'-n-heptyl-; and N'-cyclohexylmethyl-N,N'dibenzoyl hydrazines are disclosed. No biological activity is disclosed for those compounds.
In 26 J.O.C., 4336-4340 (1961), N'-t-butyl-N,N'-di-(t-butoxycarbonyl)hydrazide is disclosed. No biological activity is disclosed.
In 41 J.O.C., 3763-3765 (1976), N'-t-butyl-N-(phenyl-methoxycarbonyl)-N'-(chlorocarbonyl)hydrazide is disclosed. No biological activity is disclosed.
In 94 J.A.C.S., 7406-7416 (1972), N'-t-butyl-N,N'-dimethoxycarbonylhydrazide is disclosed. No biological activity is disclosed.
In 43 J.O.C., 808-815 (1978), N'-t-butyl-N-ethoxycarbonyl-N'-phenylaminocarbonylhydrazide and N'-t-butyl-N-ethoxycarbonyl-N'-methylaminocarbonylhydrazide are disclosed. No biological activity is disclosed for those compounds.
In 39 J. Econ. Ent., 416-417 (1946), certain N-phenyl-N'-acylhydrazines are disclosed and evaluated for their toxicity against coding moth larvae.
The N-substituted-N'-substituted-N,N'-diacyl hydrazines of the present invention differ from known compounds primarily by their N- and N'-substituents.
Compounds of the present invention are also distinguished by their excellent insecticidal activity against insects of the orders Lepidoptera and Coleoptera and particularly against insects of the order Lepidoptera, without material adverse impact on beneficial insects.